Themes > Science > Chemistry > Organic Chemistry > Common Reaction Mechanisms > Second Order Elimination: The E2 Mechanism


Secondary Elimination
generally follows the following form:

 

General Mechanism: A base attacks a Hydrogen neighboring the leaving group, pushing the electrons into the double bond as the leaving group leaves.

Rate Equation: Rate = kr[R-X][B]

Points to Watch:

Solvent Effects: Solvent polarity is unimportant. Can work in a wide variety of solvents
Substrate Effects: Highly substituted substrates work best 3 deg > 2 deg. Primary and methyl halides don't react.
Stereochemistry: Must occur with antiperiplanar stereochemistry.
Effect of Base: Base strength is important because the base is involved in the rate-determining step
Rearangements: Since E2 does not go by carbocation intermediate, no rearangements can occur.
Leaving Group Good leaving group required (ie. halide, tosylate, etc)


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